After just three games he was claimed off waivers again, this time by the Chicago Blackhawks on October 26, 2006. Stewart managed to gain more ice time and also scored his first NHL goal. Along with this achievement, Stewart was also a fan favorite among the Chicago faithful, gaining respect with his energy and relentless bodychecking. Later in the season, he moved for a fourth time when he was traded by the Blackhawks to the Tampa Bay Lightning for RussianNikita Alexeev on February 27, 2007.

After six seasons with the Tigers, Stewart left as a free agent to initially sign a one-year contract in the Austrian Hockey League with the Vienna Capitals. However two months later, Stewart terminated his contract with the Capitals and opted to end his playing career to take a scouting role within the NHL Central Scouting organization on July 30, 2015.[4]